Trimethylsilyl iodide → 1-(2-chlorophenyl)-5-[(1S,2S)-2-hydroxycyclohexyl]-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 1790042Notes

Reaction equation

HRID 1790042 reaction equation
C([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[CH2:20][CH2:19][C:18]2[N:21]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:23]([CH3:24])[C:17]=2[C:16]1=[O:40])C1C=CC=CC=1.C(O[C@H]1CCCC[C@@H]1N)C1C=CC=CC=1.ClC1C=CC=CC=1N1C2CCNCC=2C=C1C1C=CC(OC)=CC=1.C[Si](I)(C)C>C(Cl)Cl>[Cl:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[N:21]1[C:18]2[CH2:19][CH2:20][N:15]([C@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[OH:8])[C:16](=[O:40])[C:17]=2[C:23]([CH3:24])=[C:22]1[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 85247Trimethylsilyl iodideHCID 11908838(1S,2S)-trans-2-Benzyloxy-cyclohexylamineHCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineHCID 696641225-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one2×

Product 1

HCID 586651481-(2-chlorophenyl)-5-[(1S,2S)-2-hydroxycyclohexyl]-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-oneYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material for this example, namely 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one, was prepared by following the methods described in Scheme 2 and Examples 12–19, using (1S,2S)-2-(benzyloxy)cyclohexylamine as R4NH2 (Scheme 2). Then, a sample of 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.36 mmol) was dissolved in methylene chloride (5 mL). Trimethylsilyl iodide (0.054 mL, 0.396 mmol) was added dropwise and the solution was stirred at rt for 18 h. The solvent was removed and the crude material was purified by silica gel column, eluting with methylene chloride followed by methanol. The product was isolated as a white solid (40.0 mg, 24%). LC-MS m/z (MH+) 465.3, retention time 3.23 min (method 1).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by silica gel column
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-9d88810ec3fa46f2b9843685a10f101f
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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